A Travel Price Comparison for United States of America Pensacola vs. Berkshires for Vacations, Tours, and Honeymoons

Should you visit Pensacola or Berkshires?

Which is cheaper to visit? Which is more expensive for vacation?

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Pensacola and Berkshires can help you decide which place is right for you.

Where Should I go: Pensacola or Berkshires?

Pensacola

With sands as white as sugar grain and a sky devoid of grey clouds and innumerable downpours, Pensacola is known by many as the "Western Gate to the Sunshine State." Located in northern Florida, Pensacola is a waterfront city known for its pristine beaches and rich Floridian history. As one of the earliest European settlements in the U.S., Pensacola is riddled with museums and landmarks that commemorate the state's history, making the city quite appetizing for history buffs and students alike. However, if you are simply looking to get the most out of the all-around good weather of Florida, Pensacola's protected beaches complemented with high-class restaurants and stores make this a vacation capital for many.

Berkshires

The Berkshires are a popular highland destination in the western part of Massachusetts and northwest Connecticut. The region has scenic landscape, hiking, lakes, recreational opportunities and other outdoor experiences. The Berkshires also has an impressive cultural scene with music, arts, museums, and live theaters.

The Berkshires can be a bit expensive to visit if you stay at a luxury resort and take advantage of the award winning restaurants in the area. Alternatively, the experience can be equally rewarding by camping, picnicking, and spending your time hiking and enjoying the beautiful natural setting.

For some great organized tour ideas, see The Best 2-Week Tours from San Francisco, The Best 2-Week Tours from Los Angeles, The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.


Which place is cheaper, Berkshires or Pensacola?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Pensacola is $198, while the average daily cost in Berkshires is $244. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Pensacola and Berkshires in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Pensacola $115
    Berkshires $141
  • Accommodation Typical double-occupancy room
    Pensacola $230
    Berkshires $282
Compare Hotels in Pensacola and Berkshires

Looking for a hotel in Pensacola or Berkshires? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Pensacola


Hotels in Berkshires


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Pensacola Hotel Prices and Berkshires Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Pensacola $64
    Berkshires $47
Typical Local Transportation Prices in Pensacola

Below are a few samples from actual travelers for transportation costs in Pensacola:


  • Boca Grande Causeway Toll
    $5.00

Hired Cars and Shuttles in Pensacola

Some specific examples of transportation prices in Pensacola:

  • Pensacola International Airport (PNS) to Destin, FL - Arrival Private Transfer: $71
  • Pensacola International Airport (PNS) to Destin, FL - Roundtrip Private Transfer: $142
  • Pensacola International Airport (PNS) to Pensacola - Arrival Private Transfer: $55
  • Pensacola International Airport (PNS) to Pensacola - Round-Trip Private Transfer: $109
  • Pensacola to Pensacola International Airport (PNS) - Departure Private Transfer: $55

Is it cheaper to fly into Pensacola or Berkshires?

Prices for flights to both Berkshires and Pensacola change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Pensacola $48
    Berkshires $73
Typical Food Prices in Pensacola

Some typical examples of dining costs in Pensacola are as follows:


  • Two Ice Creams
    $6.00

Food Tours and Cooking Classes in Pensacola

Also, here are some specific examples of food and dining related activities in Pensacola.

  • Seville Stroll Food Tour: $72

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Pensacola $13
    Berkshires $25
Typical Entertainment Prices in Pensacola

Some typical examples of activities, tours, and entrance ticket prices in Pensacola are as follows:


  • Bike Rental
    $16

Tours and Activities in Pensacola

Some specific costs of activities, tours, and entrance tickets for Pensacola are as follows:

  • Scavenger Hunt Adventure in Pensacola by Wacky Walks: $10
  • Scavenger Hunt Adventure in Pensacola by Zombie Scavengers: $20
  • Public Dolphin & Scenic Bay Sightseeing Cruise, Pensacola FL: $30
  • Penscola Most Haunted: Ghost Tour and Scavenger Hunt: $30
  • Ghosts and Graveyard Tour of Pensacola: $34
  • Hop-on Hop-off Tour in Pensacola : $35
  • Frisky Mermaid Public Dolphin + Sightseeing Cruise Up to 49 Pax: $37
  • Pensacola Beach Jolly Dolphin Cruise and Scenic Bay Tour: $39
  • Pensacola Shared Trolley Ghost and Mystery Tour: $45
  • Seville Haunted Luncheon and Ghost Tour: $50
  • Land Paddle Tour in Pensacola: $50
  • Seville Quarter Haunted Ghost Tour, Investigation, and Luncheon: $50

Tours and Activities in Berkshires

Here are a few actual costs in Berkshires for available activities, ticket prices, and tours:

  • 2-Hour Guided Private Forest Bathing Experience Lenox: $40

Alcohol
  • Alcohol Drinks for one day
    Pensacola $44
    Berkshires $31

Sample the Local Flavors in Pensacola

Also in Pensacola, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Walking Pub Tour : $21


When we compare the travel costs of actual travelers between Pensacola and Berkshires, we can see that Berkshires is more expensive. And not only is Pensacola much less expensive, but it is actually a significantly cheaper destination. So, traveling to Pensacola would let you spend less money overall. Or, you could decide to spend more money in Pensacola and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Berkshires would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Berkshires than you might in Pensacola.

If you're trying to decide if either of these two destinations are within your price range, also see Is Pensacola Expensive? and Is Berkshires Expensive?.



When is the best time to visit Pensacola or Berkshires?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Pensacola or Berkshires in the Summer?

The summer attracts plenty of travelers to both Pensacola and Berkshires. Many travelers come to Pensacola for the beaches, the hiking, and the family-friendly experiences.

Pensacola is a little warmer than Berkshires in the summer. The daily temperature in Pensacola averages around 82°F (28°C) in July, and Berkshires fluctuates around 72°F (22°C).

Pensacola gets a good bit of rain this time of year. In July, Pensacola usually receives more rain than Berkshires. Pensacola gets 7.4 inches (189 mm) of rain, while Berkshires receives 2.7 inches (69 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Pensacola 82°F (28°C) 
    Berkshires 72°F (22°C)

Should I visit Pensacola or Berkshires in the Autumn?

The autumn brings many poeple to Pensacola as well as Berkshires. Many visitors come to Pensacola in the autumn for the hiking trails and the shopping scene.

In the autumn, Pensacola is much warmer than Berkshires. Typically, the autumn temperatures in Pensacola in October average around 69°F (21°C), and Berkshires averages at about 51°F (11°C).

Pensacola receives a lot of rain in the autumn. Pensacola usually gets more rain in October than Berkshires. Pensacola gets 4.2 inches (107 mm) of rain, while Berkshires receives 2.6 inches (67 mm) of rain this time of the year. Also, the hurricane season in Pensacola is June to November.


  • Autumn Average Temperatures October
    Pensacola 69°F (21°C) 
    Berkshires 51°F (11°C)

Should I visit Pensacola or Berkshires in the Winter?

Both Berkshires and Pensacola are popular destinations to visit in the winter with plenty of activities. Most visitors come to Pensacola for the museums, the shopping scene, and the cuisine during these months.

The weather in Berkshires can be very cold. In January, Pensacola is generally much warmer than Berkshires. Daily temperatures in Pensacola average around 51°F (10°C), and Berkshires fluctuates around 22°F (-6°C).

It's quite rainy in Pensacola. In January, Pensacola usually receives more rain than Berkshires. Pensacola gets 4.6 inches (117 mm) of rain, while Berkshires receives 1.9 inches (49 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Pensacola 51°F (10°C) 
    Berkshires 22°F (-6°C)

Should I visit Pensacola or Berkshires in the Spring?

Both Berkshires and Pensacola during the spring are popular places to visit. The spring months attract visitors to Pensacola because of the beaches.

Pensacola is much warmer than Berkshires in the spring. The daily temperature in Pensacola averages around 67°F (20°C) in April, and Berkshires fluctuates around 47°F (9°C).

Pensacola usually gets more rain in April than Berkshires. Pensacola gets 3.4 inches (87 mm) of rain, while Berkshires receives 2.6 inches (66 mm) of rain this time of the year. Keep in mind that June to November is the hurricane season in Pensacola.


  • Spring Average Temperatures April
    Pensacola 67°F (20°C) 
    Berkshires 47°F (9°C)

Typical Weather for Berkshires and Pensacola

Pensacola Berkshires
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 51°F (10°C) 4.6 inches (117 mm) 22°F (-6°C) 1.9 inches (49 mm)
Feb 54°F (12°C) 5.4 inches (137 mm) 24°F (-4°C) 2 inches (51 mm)
Mar 60°F (16°C) 5.6 inches (143 mm) 35°F (2°C) 2.5 inches (63 mm)
Apr 67°F (20°C) 3.4 inches (87 mm) 47°F (9°C) 2.6 inches (66 mm)
May 74°F (24°C) 4.2 inches (107 mm) 59°F (15°C) 3 inches (75 mm)
Jun 80°F (27°C) 6.4 inches (163 mm) 67°F (20°C) 3.3 inches (83 mm)
Jul 82°F (28°C) 7.4 inches (189 mm) 72°F (22°C) 2.7 inches (69 mm)
Aug 82°F (28°C) 7.4 inches (188 mm) 70°F (21°C) 3 inches (76 mm)
Sep 78°F (26°C) 5.3 inches (135 mm) 62°F (17°C) 2.8 inches (71 mm)
Oct 69°F (21°C) 4.2 inches (107 mm) 51°F (11°C) 2.6 inches (67 mm)
Nov 61°F (16°C) 3.5 inches (90 mm) 41°F (5°C) 2.9 inches (73 mm)
Dec 54°F (12°C) 4.3 inches (109 mm) 28°F (-2°C) 2.7 inches (69 mm)